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Amino acid communicating with polyglycol as well as manufacturing method and usage thereof

A polyethylene glycol and amino acid technology, applied in the direction of medical preparations and pharmaceutical formulas of non-active ingredients, can solve the problem of not having side chain groups and achieve the effect of improving pharmacokinetics

Inactive Publication Date: 2008-05-14
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has many limitations when used for PEGylation of small peptides: one is that the amino acids of small peptides may not have side chain groups that can bind to activated PEG

Method used

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  • Amino acid communicating with polyglycol as well as manufacturing method and usage thereof
  • Amino acid communicating with polyglycol as well as manufacturing method and usage thereof
  • Amino acid communicating with polyglycol as well as manufacturing method and usage thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Preparation of mPEG-CO-ε-NH-Lys

[0047] Reaction formula:

[0048]

[0049] Get 1g monomethoxypolyethylene glycol acid 1000 (0.001mol), 0.74g α-tert-butoxycarbonyl-L-lysine (0.003mol) and 0.62g dicyclohexylcarbodiimide (DCC, 0.003mol ) was dissolved in 100ml of dichloromethane, stirred and refluxed at room temperature for 16 hours. The mixture was filtered, and the filtrate was evaporated to dryness under reduced pressure and dried in vacuo. The obtained solid matter was dissolved in 100ml of dichloromethane, and an appropriate amount of trifluoroacetic acid was added, stirred, then concentrated by rotary evaporation at 55°C and dried in vacuo, the obtained solid matter was dissolved in 50ml of dichloromethane and dried with anhydrous magnesium sulfate, filtered and then 100ml of cooled diethyl ether was added to the filtrate, and the resulting precipitate was filtered and dried in vacuo. 1.52 g of the product mPEG-CO-ε-NH-Lys was obtained.

Embodiment 2

[0050] Example 2: Preparation of mPEG-CO-His

[0051] Reaction formula:

[0052]

[0053] Dissolve 1 g of monomethoxypolyethylene glycol acid 1000 (0.001 mol) in 50 ml of dichloromethane, add thionyl chloride (2 ml, 0.004 mol) in dichloromethane, and stir overnight at room temperature. The mixture was rotary evaporated, and the resulting solid residue was dried in vacuo. The obtained solid matter was dissolved in 100 ml of dichloromethane, 0.77 g of α-tert-butoxycarbonyl-L-histidine (0.003 mol) and 0.6 ml of triethylamine were added, and stirred overnight at room temperature. Filtrate, add an appropriate amount of trifluoroacetic acid to the filtrate and stir, then concentrate by rotary evaporation at 55°C and dry in vacuo. The obtained solid matter is dissolved in 50ml of dichloromethane and dried with anhydrous magnesium sulfate. After filtering, add 100ml of cooling diethyl ether to the filtrate. The resulting precipitate was filtered and dried in vacuo. The product m...

Embodiment 3

[0054] Embodiment 3: Preparation of mPEG-CO-Trp

[0055] Reaction formula:

[0056]

[0057]Dissolve 4 g of monomethoxypolyglycolic acid 4000 (0.001 mol) in 50 ml of dichloromethane, add thionyl chloride (2 ml, 0.004 mol) in dichloromethane, and stir overnight at room temperature. The mixture was rotary evaporated, and the resulting solid residue was dried in vacuo. The obtained solid matter was dissolved in 100 ml of dichloromethane, 0.91 g of α-tert-butoxycarbonyl-L-tryptophan (0.003 mol) and 0.6 ml of triethylamine were added, and stirred overnight at room temperature. Filtrate, add an appropriate amount of trifluoroacetic acid to the filtrate and stir, then concentrate by rotary evaporation at 55°C and dry in vacuo. The obtained solid matter is dissolved in 50ml of dichloromethane and dried with anhydrous magnesium sulfate. After filtering, add 100ml of cooling diethyl ether to the filtrate. The resulting precipitate was filtered and dried in vacuo. 4.12 g of the pro...

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PUM

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Abstract

The invention relates to an amino acid bound with polyethylene glycol with the following general structure: R-PEG-CO-X-amino acid or R-PEG-X-amino acid; wherein, PEG represents for polyethylene glycol chain; R represents for a hydroxyl group or an oxyl; the oxyl can be chosen from the C1 to C12 alkoxy, cycloalkoxy or aralkoxy; wherein, X represents for the heteroatom with active hydrogen removed except Alpha-carboxyl and Alpha-amino group in amino acid. Utilizing the amino acid bound with polyethylene glycol to synthesis polypeptide, the polypeptide is made from polypeptide positioned on specific position, not only improving the pharmacokinetics, but also having no effect of original treatment. The invention discloses the production method for the amino acid bound with polyethylene glycol.

Description

technical field [0001] The invention relates to an amino acid linked to a long chain of polyethylene glycol, its preparation method and its use in the synthesis of polypeptides, and is used to prepare polypeptides with long chains of polyethylene glycol. Background technique [0002] With the development of biotechnology, more and more small peptides with biological activity have been found to have therapeutic effects by researchers, such as: thymosin, somatostatin, angiotensin, ajirelin and so on. However, small peptides also have many disadvantages in clinical application, such as prone to immune rejection, poor stability, and faster clearance in the body. Therefore, people have adopted various methods to eliminate the above-mentioned unfavorable factors, one of which is to adopt pegylation technology. [0003] PEGylation PEGylation, also known as chemical modification, is one of the most important technologies in molecular altering structure chemistry (MASC). The resear...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K47/34C08G65/333C08G65/48A61K47/18A61K47/60
Inventor 姚文兵田浤高向东陈阳建宋潇达
Owner CHINA PHARM UNIV
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